#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006274.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006274
loop_
_publ_author_name
'Mague, J. T.'
'Vang, S.'
'Berge, D. G.'
'Wacholtz, W. F.'
_publ_section_title
;
 Isomerism/Tautomerism in Hydrazones Derived from Thiophenaldehydes and
 2-Hydrazinoquinoline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              973
_journal_page_last               979
_journal_volume                  53
_journal_year                    1997
_chemical_formula_structural     'C14 H10 Br1 N3 S1'
_chemical_formula_sum            'C14 H10 Br N3 S'
_chemical_formula_weight         332.22
_chemical_name_systematic
;
2-(5-bromothien-2-ylmethylidenehydrazono)quinoline
;
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 43n 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_type_scat_source           International_Tables_for_Xray_Crystallography
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 90.000(8)
_cell_angle_gamma                90.000(8)
_cell_formula_units_Z            8
_cell_length_a                   9.5850(7)
_cell_length_b                   9.5850(10)
_cell_length_c                   29.939(4)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293
_cell_measurement_theta_max      16
_cell_measurement_theta_min      10
_cell_volume                     2750.6(5)
_computing_cell_refinement       CAD4_software
_computing_data_collection       CAD4_software_(Enraf-Nonius,_1989)
_computing_data_reduction        PROCESS_MolEN_(Fair,_1990)
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_publication_material  CIF_VAX_MolEN
_computing_structure_refinement  LSFM_MolEN
_computing_structure_solution    Direct_methods_(SIR;_Burla_et_al.,_1989)
_diffrn_ambient_temperature      293
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2797
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        -2.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.129
_exptl_absorpt_correction_T_max  0.29
_exptl_absorpt_correction_T_min  0.26
_exptl_absorpt_correction_type   \y_scans_(North,_Phillips_&_Mathews,_1968)
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.60
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       Octahedral
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.06
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_obs          0.026
_refine_ls_shift/esd_max         0.010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0016 Fo^4^]'
_refine_ls_wR_factor_obs         0.033
_reflns_number_observed          1809
_reflns_number_total             2415
_reflns_observed_criterion       >3.0\s(I)
_[local]_cod_data_source_file    bk1314.cif
_[local]_cod_data_source_block   3
_[local]_cod_chemical_formula_sum_orig 'C14 H10 Br1 N3 S1'
_cod_database_code               2006274
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.0715(2) 0.0632(2) 0.0440(2) -0.0163(2) 0.0000(2) -0.0168(2)
S 0.0370(4) 0.0460(4) 0.0369(4) 0.0044(4) 0.0007(4) -0.0062(3)
N1 0.0390(10) 0.047(2) 0.0310(10) 0.0060(10) 0.0000(10) -0.0040(10)
N2 0.0400(10) 0.044(2) 0.0310(10) 0.0050(10) -0.0020(10) -0.0050(10)
N3 0.0330(10) 0.049(2) 0.0290(10) 0.0030(10) 0.0020(10) 0.0010(10)
C1 0.050(2) 0.046(2) 0.030(2) -0.007(2) -0.002(2) -0.002(2)
C2 0.033(2) 0.058(2) 0.048(2) -0.001(2) -0.008(2) -0.003(2)
C3 0.043(2) 0.047(2) 0.048(2) 0.010(2) -0.002(2) -0.008(2)
C4 0.038(2) 0.041(2) 0.0330(10) -0.0010(10) 0.0030(10) 0.0020(10)
C5 0.040(2) 0.043(2) 0.035(2) 0.006(2) 0.004(2) -0.005(2)
C6 0.036(2) 0.047(2) 0.0270(10) 0.0010(10) -0.0010(10) -0.0030(10)
C7 0.049(2) 0.054(2) 0.034(2) 0.009(2) -0.001(2) -0.008(2)
C8 0.055(2) 0.056(2) 0.044(2) 0.021(2) 0.008(2) -0.001(2)
C9 0.039(2) 0.043(2) 0.039(2) 0.004(2) 0.001(2) 0.009(2)
C10 0.040(2) 0.053(2) 0.057(2) 0.008(2) 0.001(2) 0.008(2)
C11 0.036(2) 0.062(2) 0.062(2) 0.001(2) -0.013(2) 0.013(2)
C12 0.061(2) 0.049(2) 0.043(2) -0.013(2) -0.017(2) 0.009(2)
C13 0.045(2) 0.038(2) 0.038(2) -0.004(2) -0.003(2) 0.002(2)
C14 0.033(2) 0.041(2) 0.0310(10) -0.0010(10) 0.001(2) 0.0080(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
Br 0.15789(5) 0.10979(4) 0.230000(10) 0.05960(10) Uani ?
S -0.00274(8) -0.00077(9) 0.14709(3) 0.0400(2) Uani ?
N1 -0.1164(3) -0.1507(3) 0.05433(8) 0.0393(7) Uani ?
N2 -0.1991(3) -0.0624(3) 0.08000(9) 0.0383(7) Uani ?
N3 -0.3542(3) -0.0818(3) 0.01916(8) 0.0368(7) Uani ?
C1 0.1487(4) 0.0020(4) 0.17790(10) 0.0418(9) Uani ?
C2 0.2528(4) -0.0744(4) 0.16070(10) 0.0460(10) Uani ?
C3 0.2086(4) -0.1413(4) 0.12080(10) 0.0460(10) Uani ?
C4 0.0739(3) -0.1110(4) 0.10870(10) 0.0371(8) Uani ?
C5 0.0078(4) -0.1688(4) 0.06980(10) 0.0395(9) Uani ?
C6 -0.3184(3) -0.0353(4) 0.06070(10) 0.0366(8) Uani ?
C7 -0.4201(4) 0.0484(4) 0.08310(10) 0.0460(10) Uani ?
C8 -0.5473(4) 0.0673(4) 0.06580(10) 0.0520(10) Uani ?
C9 -0.5880(3) 0.0069(4) 0.02420(10) 0.0402(9) Uani ?
C10 -0.7219(4) 0.0130(4) 0.00640(10) 0.0500(10) Uani ?
C11 -0.7543(4) -0.0492(4) -0.03320(10) 0.0540(10) Uani ?
C12 -0.6513(4) -0.1201(4) -0.05680(10) 0.0510(10) Uani ?
C13 -0.5179(4) -0.1310(3) -0.04030(10) 0.0407(9) Uani ?
C14 -0.4865(3) -0.0679(3) 0.00030(10) 0.0349(8) Uani ?
H3n -0.296(4) -0.105(3) 0.0050(10) 0.060(10) Uiso ?
H2 0.3433 -0.0827 0.1733 0.0556 Uiso calc
H3 0.2670 -0.2017 0.1040 0.0553 Uiso calc
H5 0.0646 -0.2302 0.0528 0.0474 Uiso calc
H7 -0.3969 0.0913 0.1107 0.0547 Uiso calc
H8 -0.6128 0.1227 0.0817 0.0621 Uiso calc
H10 -0.7926 0.0618 0.0222 0.0600 Uiso calc
H11 -0.8466 -0.0442 -0.0446 0.0642 Uiso calc
H12 -0.6735 -0.1615 -0.0848 0.0617 Uiso calc
H13 -0.4484 -0.1808 -0.0564 0.0489 Uiso calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 S C4 90.4(2) ?
N2 N1 C5 114.2(3) yes
N1 N2 C6 112.0(3) yes
C6 N3 C14 124.5(3) yes
C6 N3 H3n 116.0(10) yes
C14 N3 H3n 118.0(10) yes
Br C1 S 119.7(2) ?
Br C1 C2 125.9(3) ?
S C1 C2 114.4(3) ?
C1 C2 C3 110.4(3) ?
C2 C3 C4 114.0(3) ?
S C4 C3 110.8(3) ?
S C4 C5 126.0(3) ?
C3 C4 C5 123.2(3) ?
N1 C5 C4 130.3(3) yes
N2 C6 N3 123.9(3) yes
N2 C6 C7 120.0(3) yes
N3 C6 C7 116.1(3) yes
C6 C7 C8 121.1(4) ?
C7 C8 C9 122.1(4) ?
C8 C9 C10 124.7(4) ?
C8 C9 C14 117.6(3) ?
C10 C9 C14 117.6(4) ?
C9 C10 C11 121.7(4) ?
C10 C11 C12 119.6(4) ?
C11 C12 C13 120.9(4) ?
C12 C13 C14 118.8(4) ?
N3 C14 C9 118.1(3) ?
N3 C14 C13 120.6(4) ?
C9 C14 C13 121.2(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C1 1.873(4) ?
S C1 1.720(4) ?
S C4 1.726(4) ?
N1 N2 1.391(4) yes
N1 C5 1.289(5) yes
N2 C6 1.308(5) yes
N3 C6 1.365(4) yes
N3 C14 1.395(5) yes
N3 H3n 0.74(7) yes
C1 C2 1.341(5) ?
C2 C3 1.420(5) ?
C3 C4 1.371(5) ?
C4 C5 1.436(5) yes
C6 C7 1.429(6) yes
C7 C8 1.337(6) ?
C8 C9 1.427(6) ?
C9 C10 1.392(5) ?
C9 C14 1.405(5) ?
C10 C11 1.363(6) ?
C11 C12 1.392(6) ?
C12 C13 1.375(6) ?
C13 C14 1.391(5) ?